Chesapeake VA Homes with Gazebo Exterior features

Welcome to Chesapeake, Virginia – a hidden gem nestled in the heart of Hampton Roads. Known for its rich history, vibrant community, and stunning natural beauty, Chesapeake offers a unique blend of suburban charm and urban convenience. With its expansive parks, scenic waterways, and a plethora of recreational activities, this city is perfect for families, nature enthusiasts, and anyone looking to enjoy a relaxed lifestyle.

Chesapeake is not only famous for its outdoor adventures but also for its diverse neighborhoods, each offering a distinct character and appeal. Among these, homes featuring charming gazebos stand out as a delightful option for those seeking a touch of elegance and tranquility. Imagine stepping into your backyard oasis, where a beautifully designed gazebo serves as the perfect spot for morning coffees, evening gatherings, or simply unwinding with a good book. These exterior features not only enhance the aesthetic of your home but also provide a serene space for relaxation and entertainment.

The combination of Chesapeake’s inviting community and the allure of homes with gazebos creates an ideal setting for both new homeowners and seasoned residents. Whether you’re hosting a summer barbecue or enjoying a quiet evening under the stars, a gazebo can transform your outdoor space into a personal retreat.

Explore the possibilities of homeownership in Chesapeake, VA, where your dream home with a charming gazebo awaits. Experience the perfect blend of comfort, style, and community in this vibrant city. Welcome home!

Newest Chesapeake VA Homes with Gazebo Exterior features

$995,000

6 Beds ⋅ 4 Baths ⋅ 10645935 MLS

An exceptional opportunity to own a Stephen Alexander custom home in Greystone, one of Chesapeake's premier luxury communities where homes are rarely available. This expansive executive residence blends timeless craftsmanship with the space, flexibility, and resort-style amenities today's luxury buyers seek. A first-floor bedroom with an adjacent full bath offers versatility for guests, a home office, or multi-generational living. The primary suite is a true retreat with a fireplace, sitting area, and four closets. Enjoy a private backyard oasis featuring an in-ground pool, hot tub, screened porch, gazebo, fire pit, privacy fence, irrigation well, and expanded parking for a boat or RV. Scenic walking paths enhance this sought- after community. Significant recent investments include a new roof (2026), three HVAC systems, an encapsulated crawl space, new hardwood flooring, updated bath vanities, freshly painted kitchen cabinetry, and a new oven. Schedule your private showing today!

821 Redleafe Circle, South Chesapeake

$510,000

4 Beds ⋅ 2.1 Baths ⋅ 10645829 MLS

WELCOME HOME! Tucked away on a quiet cul de sac and set on nearly an acre backing to peaceful woods, this beautifully maintained home offers the perfect blend of privacy, outdoor living, and everyday convenience. Whether you’re enjoying your morning coffee in the screened gazebo or entertaining family and friends, you’ll appreciate the peaceful setting this property provides. Inside, you’ll find stainless steel appliances, a spacious walk in pantry, a cozy gas fireplace, and thoughtful updates throughout, including a new roof installed in 2024. A transferable 2-10 Home Warranty provides added peace of mind for the next owner. Conveniently located near Interstate 64, Route 17, shopping, dining, and major military installations throughout Hampton Roads, this home offers the ideal balance of tranquility and accessibility. Don’t miss your opportunity to make this exceptional property your next home. Schedule your private showing today!

104 Bishops Court, South Chesapeake

$535,000

4 Beds ⋅ 2 Baths ⋅ 10644832 MLS

Welcome home to this beautifully updated ranch in the desirable Crossings neighborhood of Western Branch! This move-in-ready home offers 4 bedrooms and 2 full baths, including a spacious first-floor primary suite with a renovated en-suite bath. The oversized FROG serves as a 4th bedroom, home office, gym, or media room. Freshly painted throughout, the home features soaring ceilings, an open foyer, formal living and dining rooms, new flooring, stylish fixtures, and a cozy gas fireplace. The updated kitchen boasts modern cabinetry, upgraded countertops, a breakfast area, coffee nook, and updated stainless steel appliances/gas range (2025). Relax in the fully fenced backyard featuring a deck, gazebo, rock garden, and peaceful sitting areas. Attached 2-car garage PLUS a detached 2-car garage/workshop. Schedule your private tour today! * Select photos have been virtually staged to show potential furniture layouts.

2927 Crossings Drive, West Chesapeake

$660,000

5 Beds ⋅ 3.1 Baths ⋅ 10645822 MLS

Gorgeous and spacious 3500 sq ft home has been updated plus FULLY PAID OFF SOLAR PANELS! Featuring an amazing open concept floor plan with new LVP flooring, a large primary suite with an updated full bath! The home includes fresh painting throughout, newer HVAC, granite counters, a tankless water heater, a large 2 car garage, a metal fenced-in backyard, gazebo and a large 320 sq ft powered shed/workshop! Right near the heart of Greenbrier in Kemp Bridge, you don't want to miss this one!

1439 Kemp Bridge Drive, South Chesapeake

$479,900

4 Beds ⋅ 2 Baths ⋅ 10645772 MLS

Welcome to this spacious 4-bed, 2-bath home situated on a beautiful half-acre lot in the heart of Great Bridge! Offering a flexible floor plan, this home features 2 oversized living areas, 2 spacious primary bedrooms, & 2 additional bedrooms—ideal for multigenerational living, a home office, playroom, or the potential for a 5th bedroom. Updates include fresh interior paint, new flooring, restored hardwood floors, & renovated bathrooms. The updated kitchen offers new countertops, ample cabinet space, & a cozy breakfast nook. Step outside to the covered deck overlooking the expansive backyard, providing plenty of room for entertainment, gardening, pets, or future outdoor additions. Located in the highly desirable Great Bridge school district, you’ll enjoy the convenience of being just minutes from shopping, restaurants, & everyday amenities. Don’t miss this rare opportunity to own a move-in-ready home with space, flexibility, & an unbeatable location. Schedule your showing today!

145 Hurdle Dr Drive, South Chesapeake

$635,000

5 Beds ⋅ 3.1 Baths ⋅ 10645747 MLS

Beautiful 5-bedroom, 3-bath home built in 2017 and thoughtfully upgraded, located on a private cul-de-sac with a large, vinyl privacy-fenced yard. Inside, the open floor plan features LVP flooring, a gas fireplace, and a seamless flow into the remodeled kitchen, complete with quartz countertops, custom cabinetry, under-cabinet lighting, and updated appliances (2024). The kitchen complimented with a built-in breakfast nook and custom pantry, while additional custom cabinetry enhances select bedrooms. The primary suite offers a stylishly renovated bath for a true retreat feel. Come outside to enjoy the spacious, private backyard, ideal for relaxing or entertaining with gazebo patio, playground, trampoline and kids pool. The home also includes a finished 3+ car garage with epoxy floors, overhead storage, and a 240V outlet for EV/RV/generator use. Additional features include pre-wired surround sound, Cat5/TV connections in all bedrooms, an irrigation well, attic fan.

3500 Kathys Way, South Chesapeake

$699,900

5 Beds ⋅ 2.1 Baths ⋅ 10644122 MLS

Welcome to this beautifully updated 5-bedroom, 2.5-bath home in the highly sought-after Hickory school district! Major improvements have already been completed, including a new roof, both HVAC systems, windows, soffit and fascia, water heater, and deck—giving buyers added peace of mind. Inside, you'll find two tastefully updated bathrooms, spacious living areas, and a functional floor plan with room for everyone. Step outside to enjoy the fully fenced backyard featuring an above-ground pool, great for relaxing or entertaining all summer long. Conveniently located near shopping, dining, military bases, and major interstates. The sellers are relocating out of state and are looking for a quick closing. Don't miss your chance to make this move-in-ready home yours! **Updates** 2021 - upstairs air ducts, 1st HVAC, oven, dishwasher. 2022 - roof, 2nd HVAC, hot water heater, pool 2023 - windows, front door, toilets 2024 - two bathroom remodels, soffit and fascia 2025 - backyard deck

908 Bahama Way, South Chesapeake

$600,000

4 Beds ⋅ 2.1 Baths ⋅ 10643428 MLS

*Located in Butts Road Intermediate & Hickory Middle & High schools!* Welcome home to this beautifully updated 4-bedroom, 2.5-bath ranch in the desirable Ethridge Woods neighborhood! This move-in-ready home features newly installed hardwood flooring & a brand-new roof (2025/2026)! Open concept living & kitchen area that is great for entertaining. Cozy breakfast nook, wood burning fireplace in the living room, soaring cathedral ceilings in the sunroom/ office area & a huge walk in closet in the primary bedroom. So many great features throughout! Step outside to your own private backyard retreat complete with a large inground pool (liner 2018) & an expansive deck. Additional highlights include an energy-efficient geothermal heating and cooling system (2018). With its recent upgrades, exceptional outdoor living, and sought-after location, this home is ready for its next owners to move in and enjoy! (Some photos were photoshopped, but they keep their core details)

829 Donnington Drive, South Chesapeake

$950,000

5 Beds ⋅ 4 Baths ⋅ 10642562 MLS

Welcome to your own private backyard retreat! This beautifully updated home offers the perfect blend of stylish interior living and incredible outdoor entertaining. Step outside to a true backyard oasis featuring a stunning 6-foot in-ground pool with a new liner and pump, a covered lounge area, outdoor fire pit, built-in bar, outdoor kitchen with grill, and plenty of space to host family and friends all season long. A screened porch conveniently connects the outdoor living space to the home, creating seamless indoor-outdoor living. Inside, the nearly renovated kitchen is the heart of the home, showcasing gorgeous marble countertops, a spacious center island, all LG appliances, bar-height seating, and a built-in desk area great for working from home or everyday organization. The open-concept design flows effortlessly into the inviting living room, making entertaining easy. Upstairs, you'll find generously sized bedrooms with abundant closet space, including a spacious room over the garage that offers endless possibilities for a media room, playroom, guest suite, or home office. The luxurious primary suite is a true retreat, featuring a cozy sitting area with its own fireplace, an oversized walk-in closet, and a beautifully appointed en-suite bath complete with dual-height vanities, a private water closet, soaking tub, and separate walk-in shower. Light wood-look luxury vinyl plank flooring adds warmth and elegance throughout the main living areas, while plush carpeting creates comfort upstairs. Thoughtfully updated and impeccably maintained, this home offers the perfect combination of comfort, style, and resort-style outdoor living. Don't miss the opportunity to make this exceptional property your next home!

129 Greengable Way, South Chesapeake

$975,000

5 Beds ⋅ 4.2 Baths ⋅ 10642217 MLS

Experience this exceptional waterfront home, built by Sasser, in person—photos simply can't capture its beauty, scale, or breathtaking setting. From the moment you arrive, you'll be captivated by panoramic views, an abundance of natural light, and picturesque scenery surrounding the home. Inside, you'll find an expansive kitchen designed for gathering, along with the rare convenience of a full bathroom off every bedroom. The first floor features the spacious primary suite with its private bath, as well as an additional bedroom and full bathroom, offering flexible living options. Need more space? The massive attic and storage areas provide incredible potential to be finished into additional living space if desired. Step outside and enjoy everything this property has to offer. Relax on the oversized front porch that wraps around the home, entertain on the expansive rear deck overlooking the water, gather around your private bonfire pit, or stroll down to your private dock just beyond the beautifully landscaped backyard. This is a home that truly must be experienced in person to appreciate everything it has to offer. Schedule your private showing today!

3000 Miars Green, West Chesapeake

$599,000

4 Beds ⋅ 2.1 Baths ⋅ 10641342 MLS

Spacious Riverwalk home offering over 3,372 sq. ft. with 4 bedrooms, 2.5 baths, a two-car garage, 2 decks with private views of the lake. Recent improvements include gas HVAC in 2022, roof approximate 6 years old, encapsulated crawl space, Anderson windows with warranty, and new kitchen appliances. Large family room and kitchen - great for everyday life and easy hosting. Enjoy Riverwalk amenities including clubhouse, pool, playgrounds, and tennis courts. A wonderful opportunity to personalize a spacious home in a sought-after Chesapeake community. Close to the Hospital, Dining, Shopping and Interstates.

220 Marsh Island Drive, South Chesapeake

$665,000

5 Beds ⋅ 3 Baths ⋅ 10641305 MLS

All-brick 5BR home with 3,466 SF on a cul-de-sac - no HOA. Rich hardwood floors flow through the main level and into the primary suite on the second, anchoring a home that balances timeless character with everyday livability. The Large Living areas open up to the expansive backyard featuring a covered outdoor kitchen, screened gazebo, and sprawling composite deck. Lovingly maintained by one owner since 2000 and move-in ready, this Chesapeake gem delivers the space, quality, and lifestyle. Large lot | No HOA | Pride of ownership | Move-in ready.

3932 Colony Pointe Drive, West Chesapeake

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Some listings may be duplicated in the search results due to the co-mingling of listings from more than one multiple listing service. Should there be different listing information between the duplicated listings; user is advised to verify the accuracy of the listing information before making any financial decisions.